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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

N,N-Dimethylformamide dimethyl acetal (DMFDMA): from derivatisation to C1 synthon

Natalie Ferreira Araujo https://orcid.org/0000-0001-8450-326X A * and Sabrina Baptista Ferreira https://orcid.org/0000-0002-5363-0888 A
+ Author Affiliations
- Author Affiliations

A Laboratório de Síntese Orgânica e Prospecção Biológica, Departamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, 21941-590, Rio de Janeiro, Brazil. Email: sabrinab@iq.ufrj.br

* Correspondence to: nataliearaujo55@gmail.com

Handling Editor: Craig Hutton

Australian Journal of Chemistry 77, CH24020 https://doi.org/10.1071/CH24020
Submitted: 22 February 2024  Accepted: 24 May 2024  Published online: 13 June 2024

© 2024 The Author(s) (or their employer(s)). Published by CSIRO Publishing.

Abstract

N,N-Dimethylformamide dimethyl acetal (DMFDMA), also called 1,1-dimethoxy-N,N-dimethylmethanamine, is a colorless liquid with rancid odour. The chemical structure of DMFDMA presents two important sites, a partially positive carbon that acts as an electrophile in condensation reactions and a partially negative nitrogen that acts as a nucleophile. Because of its structure, DMFDMA reacts with many different organic groups and can be a versatile reagent used in gas chromatography, as a protecting group and as a C1 synthon, especially in the construction of heterocycles.

Keywords: alkylating agent, C1 synthon, enaminone synthesis, gas chromatography, heterocyclic synthesis, N,N-dimethylformamide dimethyl acetal, protecting group, selective alkyl cleavage.

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